Chester Vacation Packages

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Your Chester Vacation

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester vacation package that's customized to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like LEGOLAND® New York, The Rock Sports Complex and Goshen Historic Track. Don't delay visiting this destination any longer. Your ultimate Chester vacation is a couple of clicks away with Expedia.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
per person
Jun. 28 - Jul. 1
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (648 reviews)
Everything was okay. The breakfast needs some improvement.

Reviewed on Apr. 23, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Jun. 14 - Jun. 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
7.8/10 Good! (378 reviews)
Lots of people living here with kids

Reviewed on Apr. 1, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Jun. 4 - Jun. 8
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
8.4/10 Very Good! (1,003 reviews)
Loved the view from the rooms.

Reviewed on Apr. 22, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHG
2.5 out of 5
2 Bryle Place, Chester, NY
Fully refundable
The price is CA $165 per night from Apr. 27 to Apr. 28
CA $165
CA $187 total
includes taxes & fees
Apr 27 - Apr 28
8.4/10 Very Good! (1,000 reviews)
"I only stayed for the night but the front desk was nice and quick. Area is very quiet and peaceful."

Reviewed on Apr. 11, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Apr. 27 to Apr. 28
CA $135
CA $153 total
includes taxes & fees
Apr 27 - Apr 28
8.2/10 Very Good! (1,001 reviews)
"Great place for couples getaway"

Reviewed on Apr. 22, 2025

Overlook Lodge at Bear Mountain
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from May 1 to May 2
CA $175
CA $207 total
includes taxes & fees
May 1 - May 2
9.2/10 Wonderful! (682 reviews)
"Everything was okay. The breakfast needs some improvement."

Reviewed on Apr. 23, 2025

La Quinta Inn & Suites by Wyndham Middletown
See all 977 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination from CA $682 on Expedia. However, how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
You can typically find lower prices and better availability in January, February and March. Browse our cheap Chester vacation packages and you could land some excellent off-season deals.
How many days is enough for Chester?
We recommend booking a Chester vacation for at least 2 days. This will allow you plenty of time to check off top sights such as Castle Fun Center and The Rock Sports Complex, as well as explore neighborhoods like South Blooming Grove and Walton Park. You might even be able to slot in a day trip outside of Chester.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like The Rock Sports Complex among the many things to keep you busy. Whether you’re heading away with the family or getting away with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Finding a cheap Chester package deal is a breeze with Expedia. Once you’ve entered your destination and preferred dates under our “Packages” tab, set your budget, apply a couple of filters and browse what’s available. You can fine-tune your search by “Amenities,” “Property type,” “Guest rating” and more. Order the results by “Price: low to high” to discover the most wallet-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you have your Chester travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Chester?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the activities available will also help you decide when to vacation in Chester.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chester.
  3. Decide how many days away: Start by making a list of all the sights and activities you’d like to experience in Chester. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chester vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.